tyrosyl propionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tyrosyl propionate
• 英文别名: tyrosol propionate；4-hydroxyphenethyl propionate；2-(4-hydroxyphenyl)ethyl propanoate
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: PGQKVDCXCRDUMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tyrosyl propionate 在 Agaricus bisporus tyrosinase immobilized on polydiallyldimethyl ammonium chloride functionalized oxidized multi-walled carbonanotubes 、 氧气 、 sodium dithionite 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 24.08h， 以98%的产率得到hydroxytyrosol propionate
  参考文献：
  名称：

  Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

  摘要：

  Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.061
• 作为产物：
  描述：

  对羟基苯乙醇 、 丙酸 在 immobilized Candida antarctica Lipase B 作用下， 反应 0.25h， 以80%的产率得到tyrosyl propionate
  参考文献：
  名称：

  酶促连续流动制备受自然启发的酚酸酯作为抗自由基和抗菌剂

  摘要：

  使用来自南极假丝酵母的固定化脂肪酶 B (Novozyme 435®) 作为环戊基甲基醚 (CPME) 中的催化剂，在流动条件下通过酶促合成制备了一系列受自然启发的亲脂性酚酸酯， CPME 是一种非常规和绿色的溶剂。评估了它们对四种选定细菌菌株的抗菌活性以及它们作为自由基清除剂的效率。与母体非酯化化合物相比，所得化合物的特点是亲脂性增强，这增加了它们在食品工业中用作添加剂的可能性。

  DOI：

  10.1016/j.foodchem.2022.133195

文献信息

• 酪醇脂肪酸酯类化合物及其制备方法和应用
  申请人：通化师范学院

  公开号：CN109111362A

  公开（公告）日：2019-01-01

  本发明公开了酪醇脂肪酸酯类化合物及其制备方法和应用，属于生物医药技术领域，该酪醇脂肪酸酯类化合物是对酪醇的化学结构进行衍生化，在其结构中引入脂肪酸，其结构与酪醇相比有较大差异，且具有较好的抑菌和抗氧化作用。本发明还提供了酪醇脂肪酸酯的制备方法，即以酪醇、三苯基磷和脂肪酸为原料，氮气保护下加入四氢呋喃，0℃下滴加偶氮二甲酸二异丙酯，反应后经柱层析即得。有益效果为：本发明酪醇脂肪酸酯类化合物药物动力学性能好、生物活性高；该制备方法反应过程步骤短、选择性好，一步反应即可得到目标化合物，收率高，环境友好；该酪醇脂肪酸酯具有抑菌和抗氧化作用。
• [EN] PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES<br/>[FR] PROCÉDÉ DE PRODUCTION D'OLÉOCANTHAL, D'OLÉACEINE ET DE LEURS ANALOGUES
  申请人：NATIONAL AND KAPODISTRIAN UNIV OF ATHENS

  公开号：WO2021121925A1

  公开（公告）日：2021-06-24

  A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.

  根据公式(I)，从欧洲橄榄叶苷开始生产化合物的方法，例如欧力坎醇或欧力酮。该方法提供了欧力坎醇、欧力酮及其类似物所需立体化学结构的二醛核心。此外，通过在酯化步骤中改变醇基的结构，该方法可用于生产大量结构多样的产物。
• Synthesis of Bioactive Hydroxytyrosol Esters via Multienzyme Cascade on Electroactive Melanin Lignin Nanoparticles: A One‐Pot Approach without Extra Reducing Agents
  作者：Davide Piccinino、Valentina Ubertini、Eliana Capecchi、Elisabetta Tomaino、Valeria Gigli、Raffaele Saladino

  DOI：10.1002/cctc.202300533

  日期：2023.7.21

  A one‐pot strategy for the synthesis of bioactive hydroxytyrosol esters from tyrosol and lipophilic carboxylic acids has been developedviamultienzyme cascade immobilized on electroactive melanin lignin nanoparticles. The novel catalyst involved the co‐immobilization of lipase and tyrosinase on the polyphenolic support and was operative in the presence of sustainable 2‐methyltetrahydrofuran as organic reaction solvent. The system did not require the use of extra reducing agents for the selective synthesis of catechols. Optoelectronic and electrochemical studies suggested the role played by melanin lignin nanoparticles in the regeneration of the active site of tyrosinase from unproductivemet‐form to reversibledeoxy/oxy‐form. This effect improved the overall activity of tyrosinase in the multienzyme cascade favouring the reduction of undesired quinones to corresponding catechols.

  摘要 开发了一种以酪醇和亲脂性羧酸为原料合成生物活性羟基酪醇酯的单锅策略，该策略是将多酶级联固定在具有电活性的黑色素木质素纳米颗粒上。这种新型催化剂将脂肪酶和酪氨酸酶共同固定在多酚载体上，并可在可持续的 2-甲基四氢呋喃作为有机反应溶剂的情况下工作。该系统在选择性合成儿茶酚时无需使用额外的还原剂。光电和电化学研究表明，黑色素木质素纳米颗粒在将酪氨酸酶的活性位点从非生产性的金属形式再生为可逆的乙氧基/氧形式方面发挥了作用。这种作用提高了酪氨酸酶在多酶级联中的整体活性，有利于将不需要的醌还原为相应的儿茶酚。
• PROCESS FOR PREPARING TETRAKIS(3-(3,5-DI-tert-BUTYL-4-HYDROXYPHENYL)PROPIONYLOXYMETHYL)METHANE
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：EP0300055A1

  公开（公告）日：1989-01-25

  A process for preparing tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl)methane by conducting an ester-exchange reaction of an alkyl 3-(3,5-di-tert-butyi-4-hydroxyphenyl)propionate with pentaerythritol in the presence of a basic catalyst, which comprises conducting the reaction in the presence of an alkyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate. This process ensures preparation of tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxymethyl)-methane with good reproducibility in a high yield and as fine particles having good properties and no coloration.

  一种在碱性催化剂存在下通过 3-(3,5-二叔丁基-4-羟基苯基)丙酸烷基酯与季戊四醇进行酯交换反应制备四(3-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基)甲烷的工艺，包括在 3-(3-叔丁基-4-羟基苯基)丙酸烷基酯存在下进行反应。该工艺可确保制备四(3-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基)甲烷的重现性良好，产率高，颗粒细小，性能良好，不着色。
• Thermochromic opaque composition and uses thereof
  申请人：THE PILOT INK CO., LTD.

  公开号：EP0595577A2

  公开（公告）日：1994-05-04

  There are provided a thermochromic opaque composition capable of exhibiting change in transparency together with change in color in response to temperature variation, a laminate member employing the same, and a three-dimensional article capable of concealing and revealing the interior, utilizing the laminate member. The thermochromic opaque composition is formed by dispersing a thermochromic material, capable of developing and erasing color by an electron donating-accepting reaction, in small particles in vinyl chloride-vinyl acetate matrix resin. The above-mentioned structure realizes reversible change in transparency, together with change in color, in response to temperature variation, with hysteresis with a temperature difference of 10°C at minimum to 50°C between the high and low trigger temperatures.

  本发明提供了一种热致变色不透明组合物，该组合物能够随着温度的变化而显示出透明度的变化以及颜色的变化，还提供了一种使用该组合物的层压件，以及一种利用该层压件能够隐藏和显示内部的三维物品。 热致变色不透明组合物是通过将热致变色材料分散在氯乙烯-醋酸乙烯基质树脂的小颗粒中形成的，这种材料能够通过电子捐献-接受反应显色和消色。 上述结构可随着温度的变化实现透明度的可逆变化以及颜色的变化，并具有滞后性，触发温度的高低温差最小为 10°C，最大为 50°C。